EP0739878B1 - Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine - Google Patents

Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine Download PDF

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Publication number
EP0739878B1
EP0739878B1 EP96105509A EP96105509A EP0739878B1 EP 0739878 B1 EP0739878 B1 EP 0739878B1 EP 96105509 A EP96105509 A EP 96105509A EP 96105509 A EP96105509 A EP 96105509A EP 0739878 B1 EP0739878 B1 EP 0739878B1
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EP
European Patent Office
Prior art keywords
general formula
acid
weight
compounds
salts
Prior art date
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Expired - Lifetime
Application number
EP96105509A
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German (de)
English (en)
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EP0739878B2 (fr
EP0739878A1 (fr
Inventor
Ingo Dr. Hamann
Hans-Jürgen Dr. Köhle
Winfried Dr. Wehner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Goldschmidt Rewo GmbH
Original Assignee
Witco Surfactants GmbH
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/917—The agent contains organic compound containing oxygen
    • Y10S516/918—The compound contains carboxylic acid ester group

Definitions

  • the invention relates to a method for producing highly concentrated flowable aqueous solutions of betaines.
  • Betaines have become cosmetic in recent years Industry as an integral part of recipes, in particular for hair and body cleansing. They have the ability to form a dense and creamy foam which also in the presence of other surfactants, soaps and Additives remain stable over a long period of time with recognized good cleaning properties without any irritating side effects, even for sensitive ones Skin.
  • betaines are described in detail in the relevant patent and technical literature (US Pat. No. 3,225,074).
  • compounds containing tertiary amine nitrogen atoms are reacted with ⁇ -halocarboxylic acids or their salts in aqueous or water-containing media.
  • the alkyl radical R 3 can be derived here from the natural or synthetic fatty acids with 6-20 C atoms, preferably from the natural vegetable or animal fatty acids with 8-18 C atoms, and their naturally occurring, specially adjusted mixtures with one another or with one another.
  • fatty acids examples include caproic acid, caprylic acid, Capric acid, lauric acid, palmitic acid, stearic acid, Linoleic acid, linolenic acid, ricinoleic acid into consideration.
  • the naturally occurring fatty acid mixtures are preferred with a chain length of 8 - 18 carbon atoms, such as Coconut fatty acid or palm kernel fatty acid, which if necessary can be cured by suitable hydrogenation methods.
  • the fatty acid amide of the formula (I) in aqueous medium ⁇ -haloalkyl carboxylic acids preferably the sodium salt of chloroacetic acid, added and at a reaction for several hours at approx. 80 - 100 ° C the quaternization accomplished.
  • a minimum amount of water be present a minimum amount of water be present.
  • the commercial concentration of betaine content on this Solutions prepared in this way are therefore about 30% by weight. or below.
  • the method according to DE-PS 3 726 322 comes without organic Solvent, however, must be used for the quaternization reaction amount of water required by distillation be removed again from the reaction product, whereby before or after adjusting to the desired concentration the pH of the solution due to relatively high amounts of acid Non-skin-specific values of 1 - 4.5 must be set.
  • the reaction mixture consists of fatty acid amide and haloalkyl carboxylic acid before or during the Quaternization reaction or the solution obtained Betaine non-ionic, water-soluble surfactants in such Amounts added that the finished solution 3 - 20 wt .-% water-soluble Contains surfactants.
  • Polyoxyethylene ethers of. are used as nonionic surfactants
  • Fatty acids used, which are sufficient for water solubility Must contain 10 - 250 oxyethylene units.
  • WO-A-95/24377 (valid according to Article 54 (3) EPC) are used as viscosity regulators Mixtures of a) nonionic surfactants and / or Hydroxycarboxylic acids and polyols and optionally free ones Fatty acids or their alkali salts used. According to the present Neither polyols nor fatty acids are invented also used.
  • WO-A-95/24376 (valid according to Article 54 (3) EPC) are used as viscosity regulators Mixtures of polyols (glycerin) and free acids (Hydroxycarboxylic acids and fatty acids) in the reaction mixture used.
  • the sodium hydroxide solution is only added after completion of the reaction (quaternization) for neutralization the hydrochloric acid released during the reaction and to remove excess alkylating agents.
  • reaction mixture before or 1-10% by weight of anionic surfactants were added during the reaction.
  • highly concentrated surfactant solutions are obtained by mixing at least two surfactants with proportions of at least 5% each, which is a G phase can form.
  • the invention therefore relates to a process for the preparation of highly concentrated flowable and pumpable aqueous solutions of betaines of the general formula III
  • R 3 -CONH- (CH 2 ) m -NR 4 R 5 wherein R 3 , R 4 , R 5 and m have the abovementioned meaning, with ⁇ -halocarboxylic acids by known processes, which is characterized in that the fatty acid amide of the general formula I and the alkali / alkaline earth metal salt of the ⁇ -halocarboxylic acid before or during the quaternization reaction 0.5-5% by weight, based on the total mixture, of at least one of the compounds (Li 1+ ) a (X n- ) b , (Na 1+ ) a (X n- ) b , (K 1+ ) a (X n- ) b , (Mg 2+ ) a (X n- ) b , (Ca 2+ ) a (X n- ) b adds, where X n- is the rest of the citric acid with n 1-3 and in the
  • the amounts are between 0.5 and 5% by weight, based on the total mixture, preferably between 1.5-2.5% by weight.
  • the upper limit is not critical, however, should be too large Amounts to be avoided as they will ultimately make up the active content Reduce.
  • a further process variant consists in that the Li + , Na + , K + , Mg 2+ , Ca 2+ salts of the organic acids are replaced in whole or in part, preferably from 30 to 70% by weight
  • Compounds of the general formula (IV) which are also used in accordance with the invention are quaternization products of dimethylethanolamine, methyldiethanolamine or alkyl (C 2 -C 10 ) -dimethylamine and monochloroacetic acid, but in particular trimethylglycine or "betaine" which occurs naturally in sugar beet (Beta vulgaris).
  • These compounds can be mixed with the Salting, parallel to the salt addition or after the salt addition in Amounts of 1 - 5 wt .-%, based on the aqueous solution, the Reaction mixture are added, the total content of salt + betaine> 5 - 7 wt .-%, based on the aqueous Solution, usually brings no benefits.
  • Mixtures of 0.5-2 are preferred according to the invention % By weight salt and 0.5-5% by weight betaine.
  • the procedure is preferably such that the ⁇ -halocarboxylic acid and those with at least one alkali or alkaline earth hydroxide neutralized acid and during the reaction for several hours in an aqueous medium at 80 - 100 ° C the pH of the solution by adding a Base, preferably an alkali hydroxide, between 8-10 is kept and after the quaternization with the pH an organic acid, preferably citric acid, to pH 4.5 - 6 is set.
  • a Base preferably an alkali hydroxide, between 8-10 is kept and after the quaternization with the pH an organic acid, preferably citric acid, to pH 4.5 - 6 is set.
  • the dry matter is added by drying the material 105 ° C determined to constant weight. These values will be determined according to the standard methods of the German society for fat chemistry (DGF): B-II.
  • the acid number is a measure of that in fats and technical Free acids contain fatty acids. It gives the number Milligrams of potassium hydroxide, which is necessary to 1 gram Neutralize substance or technical fatty acids (mg KOH / g). These values are determined according to the standard methods the German Society for Fat Chemistry (DGF): D-IV 2a.
  • the ester number is a measure of that in fats and technical Fatty acids contain esters. It gives the number of milligrams Potassium hydroxide, which is necessary to 1 gram of substance or to saponify technical fatty acids (mg KOH / g). This Values are determined according to the standard methods of the Germans Society for Fat Chemistry (DGF): C-V 4.
  • GAZ Total amine number
  • TEZ tertiary amine number
  • the total amine number gives the number of milligrams of potassium hydroxide the total basicity of 1 gram of the amine compound are equivalent (mg KOH / g).
  • the tertiary amine number gives the number of milligrams of potassium hydroxide to the tertiary amine basicity of 1 gram of Amine compound are equivalent (mg KOH / g).
  • the chloride content becomes potentiometric against a standard silver nitrate solution determined. A combined is used as the electrode Silver chloride electrode used. The values are determined according to the standard methods of the German society for fat chemistry (DGF): H-III 9.
  • the end product was a clear liquid with a viscosity of 145 mPas at 20 ° C, a dry residue of 45.5% and a chloride content of 3.7%.
  • the end product was a clear liquid with a viscosity of 140 mPas at 20 ° C, a dry residue of 45.2% and a chloride content of 3.5%.
  • the end product was a clear liquid with a viscosity 90 mPas at 20 ° C, a dry residue of 45.6% and a chloride content of 3.6%.
  • the end product was a clear liquid with a viscosity of 190 mPas at 20 ° C, a dry residue of 49.8% and a chloride content of 3.9%.
  • the end product was a clear liquid with a viscosity of 120 mPas at 20 ° C, a dry residue of 45.9% and a chloride content of 3.7%.
  • the end product was a clear liquid with a viscosity of 135 mPas at 20 ° C, a dry residue of 45.3% and a chloride content of 3.6%.
  • the end product was a clear liquid with a viscosity of 100 mPas at 20 ° C, a dry residue of 40.4% and a chloride content of 3.6%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Claims (5)

  1. Procédé de préparation de solutions aqueuses fluides et susceptibles d'être pompées, très concentrées, de bétaïnes de formule générale (III) : R3-CONH-(CH2)m-N+R4R5(CH2)yCOO- où R3 représente la radical alcoyle d'un acide gras, qui peut être facultativement ramifié, peut contenir facultativement des liaisons multiples, facultativement des radicaux hydroxyle;
    R4 et R5 représentent des radicaux alcoyle identiques ou différents avec 1 à 4 atomes C;
    m peut être 1 à 3, et
    y peut être 1, 2, 3,
    par quaternisation de composés contenant un azote d'amine tertiaire, de formule générale (I) : R3-CONH-(CH2)m-NR4R5 où R3, R4, R5 et m ont la signification citée ci-dessus, avec un acide ω-halogénocarboxylique, par un procédé connu, caractérisé en ce que l'on ajoute à l'amide gras de formule générale (I) et au sel alcalin/alcalino-terreux de l'acide ω-halogénocarboxylique avant ou pendant la quaternisation, 0,5 à 5% en poids, sur base du mélange total, d'au moins l'un des composés :
       (Li1+)a(Xn-)b , (Na1+)a(Xn-)b , (K1+)a(Xn-)b ,
       (Mg2+)a(Xn-)b , (Ca2+)a(Xn-)b
    où Xn- est le radical de l'acide citrique, avec n = 1 à 3, et dans la molécule, la valeur de a+ = b . n-.
  2. Solutions de bétaïnes, préparées suivant la revendication 1, caractérisées en ce que les sels contenus dans la solution sont pour 30 à 100% en équivalents, des sels de lithium, sodium, potassium, magnésium et/ou calcium.
  3. Solutions de bétaïnes, préparées suivant les revendications 1 à 2, caractérisées en ce qu'elles contiennent :
    >35%
    en poids de composés de formule générale (III);
    1,5 à 3%
    en poids d'au moins un sel de lithium, sodium, potassium, magnésium, calcium, et
    pour faire 100
    d'eau.
  4. Procédé suivant la revendication 1, caractérisé en ce que 30 à 70% en poids des sels de Li+, Na+, K+, Mg2+, Ca2+ de l'acide organique sont remplacés par des composés de formule générale (IV) :
    Figure 00220001
    où R, R1, R2 sont des radicaux alcoyle identiques ou différents, facultativement ramifiés, contenant facultativement des radicaux hydroxyle, avec 1 à 10 atomes C, en particulier un radical méthyle, et
       n est 1 à 3.
  5. Solutions de bétaïnes suivant les revendications 2 et 3, caractérisées en ce que 30 à 70% en poids des sels de Li+, Na+, K+, Mg2+, Ca2+ de l'acide organique sont remplacés par des composés de formule générale (IV) :
    Figure 00230001
    où R, R1, R2 sont des radicaux alcoyle identiques ou différents, facultativement ramifiés, contenant facultativement des radicaux hydroxyle, avec 1 à 10 atomes C, en particulier un radical méthyle, et
       n est 1 à 3.
EP96105509A 1995-04-29 1996-04-06 Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine Expired - Lifetime EP0739878B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19515883A DE19515883A1 (de) 1995-04-29 1995-04-29 Verfahren zur Herstellung hochkonzentrierter fließfähiger wäßriger Lösungen von Betainen
DE19515883 1995-04-29

Publications (3)

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EP0739878A1 EP0739878A1 (fr) 1996-10-30
EP0739878B1 true EP0739878B1 (fr) 1998-06-10
EP0739878B2 EP0739878B2 (fr) 2002-07-03

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Country Status (5)

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US (1) US5962708A (fr)
EP (1) EP0739878B2 (fr)
CA (1) CA2174683A1 (fr)
DE (2) DE19515883A1 (fr)
ES (1) ES2118653T3 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2786781B1 (fr) * 1998-12-07 2001-02-02 Ceca Sa Compositions hydroalcooliques concentrees fluides d'alkylamidopropylbetaines de coprah ou de palmiste hydrogene
US6579904B1 (en) * 2000-09-22 2003-06-17 K.E.R. Associates, Inc. Process for making betaine transition metal complexes for use in animal feed supplements and compositions thereof
DE10207924A1 (de) * 2002-02-23 2003-09-04 Clariant Gmbh Hochkonzentrierte wässrige Lösungen von Betainen oder Aminoxiden
IT1395286B1 (it) 2009-08-19 2012-09-05 Zschimmer & Schwarz Italiana S P A Soluzione acquosa concentrata di tensioattivo anfotero, particolarmente betaina, e procedimento per la sua preparazione
ES2864951T3 (es) 2014-09-22 2021-10-14 Evonik Degussa Gmbh Emulsión que contiene esterquats líquidos y espesantes poliméricos
EP2997959B1 (fr) 2014-09-22 2019-12-25 Evonik Operations GmbH Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996025389A1 (fr) * 1995-02-16 1996-08-22 Henkel Kommanditgesellschaft Auf Aktien Concentres aqueux de faible viscosite d'agents tensio-actifs de betaïne

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GB2022125B (en) * 1978-03-02 1982-07-07 Albright & Wilson Concentrated aqueous surfactant compositions
DE3613944C1 (de) * 1986-04-24 1987-08-13 Goldschmidt Ag Th Verfahren zur Herstellung einer hochkonzentrierten,fliess- und pumpfaehigen Betainloesung
DE3826654C1 (fr) * 1988-08-05 1991-01-31 Th. Goldschmidt Ag, 4300 Essen, De
DE4040887C2 (de) * 1990-12-20 1994-05-19 Goldschmidt Ag Th Verfahren zur Herstellung fließfähiger wäßriger Dispersionen von Betainen
DE4205880A1 (de) * 1992-02-26 1993-09-02 Goldschmidt Ag Th Verfahren zur herstellung von betainen
DE4207386C2 (de) * 1992-03-09 1997-02-13 Goldschmidt Ag Th Wäßrige flüssige Lösung eines Betains mit mindestens 40 Gew.-% Festkörpergehalt
DE4334467A1 (de) * 1993-10-08 1995-04-13 Rewo Chemische Werke Gmbh Verfahren zur Herstellung hochkonzentrierter fließfähiger wäßriger Lösungen von Betainen
DE4408183C1 (de) * 1994-03-11 1995-08-10 Henkel Kgaa Verfahren zur Herstellung von niedrigviskosen wäßrigen Konzentraten von Betaintensiden
DE4408228C2 (de) * 1994-03-11 1997-02-20 Henkel Kgaa Verfahren zur Herstellung niedrigviskoser wäßriger Betaintensidkonzentrate
DE4412481A1 (de) * 1994-04-12 1995-10-19 Witco Surfactants Gmbh Verfahren zur Herstellung hochkonzentrierter fließfähiger wäßriger Lösungen von Betainen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996025389A1 (fr) * 1995-02-16 1996-08-22 Henkel Kommanditgesellschaft Auf Aktien Concentres aqueux de faible viscosite d'agents tensio-actifs de betaïne

Also Published As

Publication number Publication date
DE19515883A1 (de) 1996-10-31
ES2118653T3 (es) 1998-09-16
EP0739878B2 (fr) 2002-07-03
CA2174683A1 (fr) 1996-10-30
US5962708A (en) 1999-10-05
DE59600260D1 (de) 1998-07-16
EP0739878A1 (fr) 1996-10-30

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